Ethyl 3-oxohexanoate → Ethyl 3-hydroxyhexanoate

HRID 263378Notes

Reaction equation

HRID 263378 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[H][H]>[Ni].O1CCCC1>[OH:1][CH:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 238498Ethyl 3-oxohexanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 61293Ethyl 3-hydroxyhexanoateYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 3-ketohexanoate 50 g (0.32 mol), Raney nickel 10 g and tetrahydrofuran 500 ml were mixed, and the mixture was reacted with stirring in an autoclave at a temperature of 50° C. and a hydrogen pressure of 5 kg/cm2 for 30 hours. After removing the Raney nickel from the reactant by filtration, the filtrate was concentrated and distilled under reduced pressure to obtain racemic ethyl 3-hydroxyhexanoate 42 g (0.26 mol, 85% )

Workup

  1. customthe mixture was reacted
  2. customAfter removing the Raney nickel from the reactant
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated
  5. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-f8339409806d4a2796533b8d45c16823
Source dataset
uspto-grants-1997_07
Patent number
US05643793

Reaction notes

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